St Jimmy
by superlockedandloaded
Summary: Art and rebellion are one and the same for Castiel Milton, a street artist and activist who can't seem to avoid running into a childhood friend and his handsome partner, Officers Sam Wesson and Dean Winchester.
1. Chapter 1

"Hands in the air NOW!" shouted a voice from behind Castiel's head. He reluctantly complied, casting a vengeful glare at the half-painted wall.

"Drop the spray can." It clattered to the ground.

"Turn around, slowly." His messy black hair stuck to the sweat on his forehead as he pivoted to face his aggressor. 'Fuck me, he's hot,' the artist realized as he took in the full scope of the police officer's tall, sandy-haired frame. "Officer, I can explain -"

"Shut it, 'Novak.' You're coming with me."

...

"Sorry about that Officer Wesson, it won't happen again." Castiel smiled his biggest for the obscenely tall detective as he was escorted from the police station.

Sam snorted. "That'd better be the last time, Cas. I can't keep covering for you, you know that."

Sam Wesson and Castiel Milton had been best friends in high school. Castiel had set Sam up with his first date, his first lay, his first cigarette… Simpler times.

"Yeah, I know." Castiel's sarcastic smirk slid into something more sincere, and a little bit sad. "Thanks."

"Just…" Sam sighed. "No more vandalism."

Castiel gasped. "It's art, Sam. You don't even understand," he lisped dramatically.

Sam laughed, a deep, golden sound that rippled from his belly. It had been a long time. "Regardless of the circumstances, it really is good to see you."

Cas smiled gently. "You too." He began walking away, but spun abruptly on his heel to face the detective again. "Hey," he called. Sam looked up. "You and your partner - office romance?"

Sam stared. "I'm not gay, you know that. Neither is Officer Winchester. I have a girlfriend!"

Castiel grinned. "People change." He pivoted and sauntered away.

Sam frowned. 'No,' he thought, 'they really don't.'

...

Dean Winchester stood in the steam of his shower for a long time that night, thinking about the man with the torn t shirt and paint-smeared fingers. 'Novak.' He was a big deal in the street art community, and no one seemed to know who he was. Like a superhero. Castiel Milton. He was a good-looking guy, with that perpetual tiredness under his big blue eyes that artists all seem to have. Dean blinked, water streaming down his forehead onto his cheeks and jaw. Looking at a guy that way - a criminal, no less - was just wrong. Wasn't it?

...

Castiel sat on the edge of the concrete overlook, swinging his bare feet back and forth, gazing out at the sleepy city. Yellow streetlights flickered, and cars meandered through cozy neighborhoods. He looked down at his phone. Balthazar was hours late, as usual. The metrosexually stylish, if cripplingly alcoholic, man operated on his own schedule, much to his friends' frustration.

A pair of headlights came up the mountain highway. Castiel turned sharply to see, flicking the stub of his cigarette out over the railing. "Finally," he muttered as the car slowed to a stop. He slid his feet out from under the railing and walked towards the vehicle, shoving his phone in his pocket. "Dude, you said you'd be here two hours ago -" Castiel froze. That wasn't Balthazar's car.

The driver's side door popped open and a pair of brown sneakers stepped out onto the road. Castiel's eyes widened. Shit.

"Officer Winchester, I'm not making any trouble here."

The man turned around to face him. "Oh, I didn't see you there… What are you doing all the way out here?" he said, shutting his car door. It was a really nice car, Castiel realized. Classic.

"Is this a '69 Impala?"

"'67. You a car man?" Dean stepped around the boot of the car, letting a hand linger on her sleek black frame.

"Sort of. I did a bit of custom work for a friend. He was actually supposed to meet me here, but I guess he lost track of time."

"Boyfriend?"

"What?"

Dean coughed. "Uh, he your boyfriend? Not a ton of reasons to come up here with a person except make out and get high."

Castiel grinned wide. "So which is it for you?"

"Oh! I - um…." Even in the dark, Castiel could see a flush come from Dean's neck, up to his freckled cheeks. It was ridiculously attractive. "Nothing, I just like the view." He paused. "How did you get here? There's no car."

"Oh, I walked." Castiel shuffled his bare feet on the gravel. That wasn't entirely true. He got a ride on some guy's motorcycle, and his sandals had fallen off a mile or two back. Oh well. He sauntered forward. "Actually, I could use a ride home."

Dean swallowed and leaned back, the backs of his legs brushing the chrome bumper of the Impala.

"If that's alright with you, officer." Castiel purred, closing the gap between them. He grasped Dean's muscular shoulder. He reveled in the smell of whiskey and leather and musk.

Dean's breathing hitched and blood rushed straight to his cock, straining against his jeans. "I - I can't," he stuttered. "This is inappropriate."

Castiel looked into his eyes. Green as summer, even in the dark. "Why did you come up here? To drink? Friends don't let friends drink and drive, and I feel like we're well on our way there," Castiel teased, reaching around Dean's waist and pulling him closer.

Dean wrestled his arm away and turned around. "You don't know me, pal," he growled. Without another word, he opened his car door with a rough heave and slid inside. Within ten seconds, the Impala was pealing out onto the highway, headlights glaring against the hills.

Castiel stared, long after the car disappeared into the valley. "What the fuck was that?"

Balthazar's Camaro squealed to a stop. He stumbled out, a giggling mess in his low v-neck shirt and shorts. There was vomit on his loafers. Castiel's nose wrinkled in disgust. "Cas, how are you doing?" Balthazar hiccuped.

"I'm not sure, actually."

...

"Dean, he didn't know." Sam assured, twiddling his empty coffee cup absentmindedly. "I know Cas really well, he's not a bad person. He's an idiot, but he's not cruel."

"Yeah, I know that, but besides that, I'm not having some fag -"

"Dean…"

"He was aggressive and it was inappropriate. I mean, he's just lucky I was off-duty." Dean slumped in his seat.

Sam sighed and looked out the car window. "I just feel bad, you know? For how his life has turned out. He's really a genius at what he does."

"Are we even having the same conversation? It's illegal, what he does."

Sam paused. "Dean, I don't want you to take this the wrong way…"

"Sam…"

"… but maybe you encouraged him a little bit?"

"No! I didn't 'encourage him' Sam, your buddy is a predator. It's just how it is."

Sam bit the inside of his cheek. "Maybe. I don't know, maybe he changed since I knew him. But if yesterday was any indication, then no. He hasn't really changed." Either that or he wasn't so 'predatory' in the first place, Sam thought silently.

Dean stared out the window.

...

Castiel paced across the marble tiling. "Why am I doing this?"

"I know." Balthazar paused to take a long drag on the hookah pipe. "It's absolutely mental."

"He's a cop. He's a detective, for Christ's sake, and I'm just head over heels." Cas laughed, rubbing his hands through his hair.

Balthazar sat sagely on a large square pillow. "I think you should do it."

Castiel stared. "What? You just said -"

"Yeah, I know, it's mental, and it really is. But you've got something to live for, Cassie. Maybe he'll do good by you."

Cas chewed on his lower lip. "Yeah, maybe… I just don't know why he freaked out last night. I knew he was closeted, but I think I scared him off."

Balthazar smiled lazily and stretched. "It's up to you, but I say go for it." He began to snore, head tilted back over the side of the pillow.

Castiel sighed and picked up the hookah, dumping the still-burning coal into the ashtray. Yes, because we all know how good your judgement is, he thought as he watched the embers crackle and smoke.

...

Dean came back to the top of the hill every night for a week. He sat where Castiel sat, legs under the railing, thinking about the artist and how delicate his fingers were, imagining _those hands_ wrapped around his waist, wrapped around his hard…

Cas set his duffel bag down and checked his watch. Two minutes. He unzipped, removed, set down, uncapped. First the black, holding a board to create hard lines. He unfolded his stencil. Tape at the bottom, fingers at the top. Spray black, then yellow, then white. He shook the can, heartbeat aligned with the rattling of the bead inside. Quick and fast. A shuffle from the other end of the alley moved closer. Castiel's head snapped to the side, watching. Caps on, cans in the bag. Rip off the stencil, fold and stuff. Zip. Cas bolted down the alleyway and out onto the street.

Dean was close to coming. He imagined that the fingers around his cock belonged to Castiel, and that he wasn't alone. He didn't want to be alone anymore. He could practically see his face, those blue eyes, that mouth coming near his. Kissing those lips… "Oh _Cas_…" he moaned, spurting all over his fingers.

...

"Late night?" Sam asked, handing Dean a cup of coffee.

"Yeah, got caught up doing something."

Sam looked at him closely. Something was different, but he couldn't place what it was. "Anyway, our good buddy Novak struck again. But he didn't leave an anarchic or antagonistic message. Honestly, I really like it." Sam handed Dean a photograph.

Dean stared.

"I don't think it's a big deal, and neither does Chief Singer, he just figures if we catch him in the act, then that's that. As it is, we can't reliably pin this on anyone."

The painting was beautiful, a nighttime cityscape from above. Streetlights glowed in the valley, and there was a rail in the foreground like the ones on the highway. There was even a classic car parked. . . oh.

"Hey, if I wanted to ask some questions, where would I find him?"

Sam thought. "As far as I know, he doesn't really have an address. Last he told me, he was staying with his friend. . . Is this for police business, or personal?"

Dean's neck flushed. "I can tell you anything, right? I mean, we're like brothers."

"Of course," Sam assured, touching his shoulder.

Dean took a breath. "Sam, I think I might be. . ."


	2. Chapter 2

_Bzzz. . . _

Balthazar scratched his three day stubble. "Coming," he mumbled. He patted the wall, finally finding the intercom button after a few tries. "Hello?"

A deep voice crackled over the intercom. "Hi, I'm looking for Castiel Milton? Does he live at this residence?"

Cas poked his head out of the kitchen. "Dean's _here_?" he mouthed.

Balthazar shushed him and pressed the intercom. "Yes, come right up." He smiled bemusedly and shuffled back into his bedroom.

"Oh, for fu -" Castiel hurried around the room, picking up bits of aluminum foil and a large glass bong in the corner, stashing them in a cabinet.

The knock at the door was so gentle, so uncertain and shy, that Castiel wasn't sure if that's what it was. He brushed off his hands and went to the peephole. Sure enough, Dean Winchester was standing there in a plaid shirt and jeans, rubbing his neck. With a deep breath, Castiel swung the door open.

"Hello, Dean."

Dean took Castiel's face between his hands. "I need you, Cas," he groaned into his open mouth.

A kiss.

Cas broke away after a moment and stared. "Okay."

Gasping breaths tore through the heavy air. Hands worked their way under shirts, pulling them up and over, liberating muscle and sweat and need. They stumbled into Castiel's bedroom, barely closing the door before fingers fumbled with buttons and zippers.

"Cas. . ."

"Hush, baby," Cas cooed, nuzzling his face into the space between Dean's neck and shoulder. He undid Dean's jeans and hooked his thumbs around the band of his boxers, pulling until they snapped back against the soft skin of his pelvis.

Dean groaned deep in his throat, sending shivers along Castiel's skin. "Please," he begged.

Castiel's lips pressed against the hollow under Dean's ear, dragging up around his earlobe. "_Please what?_" he whispered, moving down his neck, kissing, licking his collarbone.

Dean gasped, unable to speak, caught up in the sensuality, the need of it. His fingers grasped Cas's hips, pulling, grinding them against his own, feeling that throbbing in both of them. This was completely new to Dean; he had been with girls, too many girls, and he hadn't considered being with a man for such a long time. But the sameness of their bodies felt so natural, Dean realized as Castiel's tongue grazed his nipple. "Please," he repeated. "Please fuck me."

Castiel looked up. God, Dean was beautiful. Calmly, reverently, Castiel kissed Dean, marveling at the softness of his lips, the dusting of freckles across his nose, the bump there where it must have been broken and set badly. He was a miracle, and Castiel would pray that night for forgiveness for every time he had wasted himself on a man who wasn't Dean Winchester. "No," he breathed. "Fucking is blind. I want to make love to you."

As soon as he said it, Castiel wondered if it had been a mistake.

Dean froze for a second, processing. Did he really say the word 'love?' But it felt right, somehow. He caressed Castiel's cheek with the pad of his thumb. "Okay."

Castiel's palm moved against Dean's cock. It was unbelievably hard, twitching with want under the soft fabric of his boxer briefs. His fingers massaged, teased, pulled. Dean whimpered, grinding his hips into Castiel's hands.

Dean fought the instinct to close his eyes, instead meeting his partner's piercing blue gaze. The head of Castiel's cock, red and leaking, peeked out over the unbuttoned top of his jeans. Dean reached out and hesitantly brushed the top with his thumb.

Cas groaned audibly, hands curling around Dean's boxers and pulling them down to his ankles. His knees hit the hardwood floor and he grasped the back of Dean's thighs, leveling his mouth with Dean's beautiful, thick cock.

"Shit, Cas…" he gasped, threading his fingers through Castiel's messy dark hair. Cas pressed his tongue against the underside of his throbbing shaft and sucked, pulling him inside his warm, wet mouth. In, out, in… "Shit. Cas, I'm gonna…"

Cas released him with a soft 'pop'. "It's okay baby," he moaned, kissing the tip of the shaft. He took him inside his mouth again, swirling his tongue against the sensitive slit, applying more pressure until he opened his jaw further and took Dean's entire length into his throat. Dean cried out, hips spasming with pleasure.

Castiel coughed, choking around Dean's thick cock and the spurts of warm cum that hit the back of his throat. Thank god he didn't have a gag reflex. Dean withdrew and Cas swallowed, grinning. "God, you taste as good as you look," he said, pulling Dean onto the bed. The cool sheets felt good on his dewy skin. Dean held Castiel on top of him and caressed his face, marveling at its perfection.

Cas arched his back. "We don't have to do anything more," he whispered, guiding Dean's legs so he fit between them. His cock pressed into Dean's soft stomach. Dean closed his eyes and groaned. "I want you inside me, Cas."

Castiel nodded, stomach fluttering nervously. He reached over to the nightstand and grabbed a condom and a bottle of lubricant, pumping a few drops onto his fingertips.

"This might be… weird, especially since it's your first time." Cas rubbed his fingers together, pausing for a moment. "This is your first time with a guy, right?"

Dean nodded.

A finger.

A gasp.

Castiel moved slowly, building Dean's resistance to the initial discomfort of unfamiliarity, until he was rubbing two slick fingers against his prostate.

Dean's thighs quivered uncontrollably. He was erect again, throbbing against his soft stomach, the hard shaft echoing the heat and arousal inside. Castiel's other hand reached from behind and curled around his cock, pumping slowly, mercilessly. "Please, Cas. I need you." The fingers slid away. Dean groaned, arching his back.

Castiel tore the condom wrapper open with his teeth, careful not to puncture the latex inside. With one hand, he rolled it onto his stiff cock. "Just relax, baby," Cas purred, pulling his fingers out of Dean's ass and lining himself up against Dean's smooth, freckled skin. He pumped a few drops of lube onto his fingers and rubbed.

Cas pushed into Dean.

The warmth and _tightness _of him. "Jesus," he breathed, sinking deeper into Dean as slowly as he could. "You're so... _oh_..."

"Oh my god. Oh _god_..." Dean moaned, rocking his hips to meet Castiel. His erection slapped against his stomach as they crashed together and pulled apart, together, apart. Dean's eyes clenched shut. He wanted to memorize this moment, the way Cas moved inside him, the way they fit. He felt like red-hot steel, and it was hard not to cry out in pain and ecstasy with every slap of their skin, every bounce of the mattress on its springs. Before long, his inhibitions disappeared.

"Cas, you feel _amazing... oh... OH..."_

Castiel clenched his teeth and watched himself pump in and out of Dean. He is so beautiful, Cas thought as his hands roamed across the suntanned expanse of Dean's well-muscled back. He wanted to count his freckles, kiss each one and give it a name.

"_Cas..._"

Heat curled inside his belly and his balls tightened. He wanted to come so badly.

"_CAS..._"

"Wait, Dean, wait." Cas pulled out and gripped Dean's shoulder. "Would you flip over for me, babe?"

Dean's breath hitched. He nodded and rolled onto his back, spreading his legs. Cas leaned in and kissed him. Deep, sweet, passionate. "I told you I was going to make love to you," he whispered, his gaze flickering back and forth, not wanting to miss anything, catching every movement of Dean's vividly green eyes, his long blond lashes fluttering, the sweat beading on his brow.

Dean leaned in closer, hooking his thumbs into Castiel's belt loops and pulling them down. Cas looked down and stopped his hands, flushed.

"Not now, Dean."

Dean sat up. "I promise, whatever it is that you're hiding, it's fine," he assured, running his fingers through Castiel's sweaty hair.

"I can't." His forehead creased with anxiety and his eyes clenched shut. "Just... just let me keep them on, _please_."

Dean stared. He had never seen anyone so... _raw_. "Okay," he mumbled against Cas's trembling lips. His hand guided Castiel to his entrance. "I still want you, Cas. I need you."

Cas nodded and thrust himself inside, working out his frustration, his pent-up tension and pushing it inside Dean. Dean gladly accepted, pulling Cas further into him, absorbing him. He kissed Castiel's neck, sucking on his clavicle as Cas pounded him into the bed, grinding against the bundle of nerves inside. Dean wrapped his legs around his partner's thin, angular hips.

"Cas, I think… oh… I'm going to come."

Cas closed his eyes. "Me too, ungh, come with me… Ungh!"

Dean gasped at the sudden rush of heat inside. His own erection exploded, painting his stomach milky white. Cas collapsed on top of Dean, panting, sweaty, exhausted.

"Cas?"

"Hmm?" Castiel pulled out slowly, hesitant to leave Dean's warmth and tightness.

Dean bit the inside of his cheek. "Never mind."

Cas rolled onto his back and pulled off the condom, tying the top off and tossing it to a garbage bin on the other side of the room. He missed.

Dean stared at the ceiling.

Cas sat up and buttoned the top of his jeans. He walked to the corner of the room, picked up the condom, and dropped it into the bin.


	3. Ten Years Ago

**Ten Years Ago**

"Mom? Mom, I'm sorry. I'm so sorry, Mom. Mom?"

Castiel whimpered into the phone, tears streaming down his face onto his day-old clothes. He didn't care that the jail telephone was ancient, that it smelled like vomit and sweat and metallic grit, that the police officer was waving at him, mouthing "Wrap it up, Milton." He just needed to hear her voice. He just needed to know that it wasn't just a desperate plea for affection, that she didn't actually do it. The receiver clicked and the dial tone echoed in his ears, buzzing like a tattoo machine, pounding out her message loud and clear.

"Time's up." The policeman tapped his coffee-stained clipboard on the desk.

Castiel hung the phone on the hook and wiped his eyes with his sleeve. "Officer, I need to report an emergency," he choked.

...

"Naomi Milton nurtured her flock as the Lord nurtured her. He has welcomed her into his arms..."

Castiel stared at the coffin, Brother Raphael's words washing over him like rain: pale, meaningless, cold. Minutes passed, maybe hours. The sky overhead remained bright blue and cloudless. It almost seemed cruel.

A touch.

"Cas, are you going to be able to drive?"

Anna took Castiel's hand in hers. The simple action startled Castiel; they hadn't touched since, Jesus, when had it been? Before she left for school three years ago, they had embraced. Just for a second, and their mother had broken them apart with an icy glare.

Castiel shook his head. "I'm not really in a state to do much of anything," he mumbled dully.

...

The thin blade felt cool in his hand. He breathed calmly.

In.

Out.

In.

Out.

...

Blood soaked through his jeans as he walked, dodging students and open locker doors. He felt the heat of many eyes, but he didn't care. Why should he?

"Look who finally got his period!" The jeering laughter came from behind, but Castiel did not turn around. He would not react. It was just what Michael wanted.

"Fag."

Castiel's stomach turned and he stopped in his tracks. He closed his eyes and tried to breathe.

In.

Ou-

A meaty hand pulled his shoulder, slammed him against the lockers with a metallic _bang_. "Did you hear what I fucking said?" Michael hissed, hot breath hanging in a smoky fug over Castiel's face. "You're a fucking faggot, Milton."

Out.

In.

"Is that why your mom killed herself? Because I would've -"

Castiel's eyes glazed over with a boiling rage. The next seconds were a blur of fists and fingernails, shrieks and yells, red-hot and furious.

* * *

Dean Winchester pressed his lips to his flask as his legs swung, nestled under the railing of the mountain pass. "Here's to you, Dad." He held the flask out over the edge and poured. "Fucking idiot."

His father John had died on Dean's twenty-first birthday. He was driving home from the bar where they celebrated the occasion because Dean had managed to reconnect with an attractive girl from his high school, and what's a father to do? So he went home by himself. He'd had too much to drink, and it was rainy. The car hydroplaned, caught the railing, and they found him a few hours later, with a broken neck and ribs that had pierced his lungs and heart. The coroner couldn't determine which of the two killed him.

Fucking idiot.

* * *

Sam Wesson ran his fingers through his shaggy hair, shaking uncontrollably. "Oh my god, oh my god..." he moaned, pacing back and forth, rubbing his cheeks, trying to feel something, anything, that wasn't panic. "I'm sorry," Sam croaked, eyes darting between Castiel's eyes, wanting desperately for him to look up, to say something. Anything.

"I did what I did," he finally responded, still not meeting Sam's anxious gaze. He stared at the floor. There was a spot of paint there that never washed out of the carpet, no matter how many times his mother sent him to his room to scrub it clean. She kept a perfect house. White furnishings that were never to be sat upon. White dishes that were thrown away when they became cracked or stained. The corner of his mouth twitched. Perfect children who were never told that they were loved.

Sam began crying. "I am so sorry," he repeated. "I didn't mean for any of this to happen, you have to believe me," he begged, falling to his knees.

"Listen to me, Sam." Castiel sat on the floor next to him. "It's not your fault. I chose to be the one the cops went for. You don't need something like possession on your record." He stared into Sam's eyes, shining and red with tears. "You still have a future now. A clean slate. You can be anything," he murmured, wrapping his thin arms around Sam's lanky frame. A recent growth spurt had put Sam a full four inches taller than Castiel. It felt like embracing a stranger. "You can leave this shithole of a town."

Sam nodded and sobbed silently, chest shaking.

"There, there," Cas murmured, resting his head on Sam's shoulder. "Just let it out."


	4. Thirteen Years Ago

**Thirteen Years Ago**

"Dean? Dean Winchester?"

Dean spun around, nearly knocking over his beer. A gorgeous redhead stood there, clutching a white purse. Her cream dress hugged her slim figure, accentuating her toned stomach and thighs. Wow.

"I thought that was you," she said, pushing the leather jacket off the seat adjacent and waving to the bartender.

He blinked hard, head fuzzy with whiskey and a really excellent craft brew. "I'm sorry, I'm a bit buzzed right now..." he mumbled, looking her up and down appreciatively.

She grinned. Even her teeth were perfect. "I wasn't sure you'd recognize me," she continued, unfazed. "Anna. Anna Milton? We had a few classes together in high school."

Holy fuck. She had changed a lot since graduation. Not that Dean had paid much attention to her, but he did remember her gangly limbs, her awkward gait... She'd had a slight lisp from her braces. Now, she was the very vision of sleek sophistication. "Yeah, they called you Anna Wilton, didn't they?"

Fuck. Why did he bring that up? Damn alcohol.

Her face fell, and she shifted in her seat. Dean noticed his dad stand at the other end of the room; he had gone over there to talk to one of his poker buddies, but they must be leaving.

"You know what? Forget I said anything," he stuttered as Anna picked up the drink the bartender set down. Vodka and... something. Jesus, he was drunk. "Are you living in town, or...?"

Anna plucked out the tiny straws and took a sip, red lipstick marking the rim of the glass. "I'm leaving for school tomorrow," she answered, a bit louder than before. Was it louder? It sounded louder.

"Is that so?" Dean grinned, mentally preparing himself. You know the drill, Dean. End of the world speech, here we come. He opened his mouth but was interrupted. John clapped a heavy hand on Dean's back.

"Hey there! Hope my boy's not bothering you, miss," John slurred.

Anna smiled. "Not at all. In fact, we were just about to go to my place."

Dean blinked, suddenly alert. "We were?"

"Yes."

"Okay," Dean mumbled.

John grabbed his jacket from the bar, fishing out his car keys from the pocket. "I'll see you later, then." He turned, stumbling into a barstool.

"Sir? Are you sure you should be driving?" Anna called, eyebrows knitted together with concern.

"I'm fine."

Dean watched him as he walked out, fumbling with his keys in the parking lot. "He's kind of a career drunk driver," he muttered, taking a deep swig of beer. "Our house isn't far, he'll be alright."


End file.
